Abstract
2-Substituted or 2,2-disubstituted 4,6-dioxo-1,3-dioxanes, which are analogs of Meldrum's acid and were obtained by reaction of malonic acid with acetic anhydride and the appropriate carbonyl compound in the presence of sulfuric acid, exist in solution preferably in a single form according to the PMR and 13C NMR spectral data. Fluctuation of the CH2 group is not observed. The mass spectra are characteristic and are distinguished by splitting out of the carbonyl compound from the molecular ion or successive splitting out of CO2 and ketene molecules. The Meldrum acid analogs do not affect plant growth but have a depressive effect on the central nervous system of animals and low toxicity.
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Literature cited
A. N. Meldrum, J. Chem. Soc., 93, 598 (1908).
D. Davidson and S. A. Bernhard, J. Amer. Chem. Soc., 70, 3426 (1948).
M. Eigen, C. Ilgenritz, and W. Kruse, Ber., 98, 1623 (1965).
F. J. Kunz, P. Margaretha, and O. E. Polansky, Chimia, 24, 156 (1970)
E. Ott, Ann., 401, 176 (1913).
J. Swoboda, J. Derkosch, and F. Wessely, Monatsh. Chem., 91, 188 (1960).
M. I. Kabachnik, S. T. Ioffe, E. M. Popov, and K. V. Vatsuro, Tetrahedron, 12, 76 (1961).
B. Eistert and F. Geiss, Tetrahedron, 7, 1 (1959).
E. P. Klimovitskii, L. K. Yuldasheva, B. A. Arbuzov, Izv. Akad. Nauk SSR, Ser. Khim., 1574 (1973).
D. Köberl and O. E. Polansky, Monatsh. Chem., 104, 1421 (1973).
I. Schuster and P. Schuster, Tetrahedron, 25, 199 (1969).
K. Pihlata and M. Sello, Acta Chem. Scand., 22, 3053 (1968).
N. N. Mel'nikov, and Yu. A. Baskakov, Chemistry of Herbicides and Plant-Growth Regulators [in Russian], Roskhimizdat, Moscow (1962).
N. S. Vul'fson, Zh. Obshch. Khim., 20, 425 (1950).
I. N. Khaimov, Trudy Tadzhiksk. Sel'skokhoz. Instit., 1, 33 (1958).
N. S. Vul'fson, Zh. Obshch. Khim., 20, 435 (1950).
G. Swoboda, G. Adametz, J. Swoboda, and F. Wessely, Monatsh. Chem., 95, 1283 (1964).
S. I. Zav'yalov, Izv. Akad. Nauk SSR, Otd. Khim. Nauk, 2185 (1961).
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 11, pp. 1482–1486, November, 1975.
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Kost, A.N., Khaimov, L.N., Dzhurakulov, Y. et al. Meldrum's acid and its analogs. Chem Heterocycl Compd 11, 1263–1266 (1975). https://doi.org/10.1007/BF00474450
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DOI: https://doi.org/10.1007/BF00474450